27 Hilariously Awkward Family Photos

Funny Family Photos, Vintage and Weird

Say, “Cheese!” or “Geez, These Pictures are Awkward!”

Dish yourself up a plate full of the strange and uncomfortable. This crazy album of awkward family photos and oddball humor probably won’t leave you with a bad taste in your mouth. Rather, you’ll only experience bouts of head shaking and blowing air through your nose, you know, that weird form of laughter you get when you look at funny pictures on the internet. Enjoy.


Meet the McKinseys – The Royal Family of Rocheport, Missouri.

vintage family photo, 1970s fashions and ginger hair


Awkwarf funny family photo of little kids holding fish they caught, little brother hass live fish in his mouth


When anything but dad will do.

awkward family photos and portrait of mom and daughters posing with cardboard cutout of Eddie Murphy


Don’t laugh. Their first idea was to wear matching polka dot dresses.

Vintage prom photo and yearbook photo, 1970s, awkward couple wearing matching plaid tuxedos


It wasn’t that Helen couldn’t stand her husband’s snoring. She just couldn’t stand him.

Vintage family vacttion picture of mom sleeping in hotel bathroom tub becasue of dad's snoring


Even at her tender age, Allison had her “come hither smile” down pat.


It all comes down to who’s haunting whose soul.



vintage family photo of grandma with big hair, 1960s


When Picture Day discriminately falls on Hump Day.

Awkward, funny family photo of boy with 2 rabbits humping in the background


Why we never eat at Aunt Judy’s.

strange vintage family photos of two grandmas with knives and an alien strapped down on kitchen table, alien autopsy.


Shortly after Kevin was warned not to play his Nickelback medley one more time…

awkward funny photo of man passed out with a guitar broken over his head


Grandma Pearl always believed in being prepared.
funny picture of grandma on plane reading a book 5 steps to murder


Awkward family photo of married couple with husband wearing shorts in the portrait.


funny picture of dogs hounding a man sitting on the toilet


Vertical or horizontal never mattered. When Becky found a pole, she was going to work it.
vintage family photo of woman in sexy dress posing on star railing, 1960s


Sylvia never left the house without her emergency jar of mayo.
Funny family photo. Woman riding on a bus eating a jar of mayonnaise.


Though she hoped to win Best Hair, Lisa never-the-less accepted her superlative with grace.
Awkward vintage photo of girl graduating high school in 1981


Funny family photo portrait of dad in karate uniform holding son upside down


Franklin finally found the job in which he’d excel.
Funny picture off man passed out in chair begging for money with cardboard sign that says, "shitty advice $1."


uncomfortable awkard funny family pic of brother and sister wearing Happy Days Fonzie Socks in the 1970s


Awkward funny family vacation photo of women on the beach with a man performing a ball check in the background


Let judgement day begin and haunt you through all eternity.
Awkward family photo of kids with mom and dad's silhouettes look down upon them


FFunny family photo of boy walking to school in matching pepperoni piza shirt, hat and backpack


vintage color snapshot photo of women phosing with futuristic astronauts in Tomorrowland at Disney Land


The day Tyler regretted finding a roommate on Craigslist.

awkward photo of roommates, kid with vacuum cleaner hose on his boob


The birthday Kimmie will never forget in her nightmares.
vintage funny family photo of screaming girl being held by creepy clown

27 Hilariously Awkward Family Photos 1

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